CN1295997A - 利用配体混合物由烯烃催化制备醛的方法 - Google Patents

利用配体混合物由烯烃催化制备醛的方法 Download PDF

Info

Publication number: CN1295997A
Authority: CN; China
Prior art keywords: carbon atom; aliphatic series; unsubstituted; aromatic hydrocarbyl; formula
Prior art date: 1999-11-12
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.): Pending

Application number

CN00132364A

Other languages

English (en)

Chinese (zh)

Inventor

D·赫斯

D·勒特格尔

D·赛伦特

A·贝尔纳

Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)

OKSENNO OLEFIN CHEMICAL GmbH

Original Assignee

OKSENNO OLEFIN CHEMICAL GmbH

Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)

1999-11-12

Filing date

2000-11-13

Publication date

2001-05-23

2000-11-13 Application filed by OKSENNO OLEFIN CHEMICAL GmbH filed Critical OKSENNO OLEFIN CHEMICAL GmbH

2001-05-23 Publication of CN1295997A publication Critical patent/CN1295997A/zh

Status Pending legal-status Critical Current

Links

230000003197 catalytic effect Effects 0.000 title claims abstract description 9
238000000034 method Methods 0.000 title claims description 42
125000002485 formyl group Chemical class [H]C(*)=O 0.000 title claims 2
239000003446 ligand Substances 0.000 title abstract description 30
239000000203 mixture Substances 0.000 title description 40
150000001336 alkenes Chemical class 0.000 claims abstract description 57
125000004432 carbon atom Chemical group C* 0.000 claims abstract description 48
238000007037 hydroformylation reaction Methods 0.000 claims abstract description 40
125000001931 aliphatic group Chemical group 0.000 claims abstract description 33
229910052751 metal Inorganic materials 0.000 claims abstract description 21
239000002184 metal Substances 0.000 claims abstract description 21
125000005842 heteroatom Chemical group 0.000 claims abstract description 16
229910052698 phosphorus Inorganic materials 0.000 claims abstract description 14
229910052785 arsenic Inorganic materials 0.000 claims abstract description 11
229910052760 oxygen Inorganic materials 0.000 claims abstract description 11
229910052787 antimony Inorganic materials 0.000 claims abstract description 10
229910052717 sulfur Inorganic materials 0.000 claims abstract description 10
229910052801 chlorine Inorganic materials 0.000 claims abstract description 7
229910052731 fluorine Inorganic materials 0.000 claims abstract description 7
229910052757 nitrogen Inorganic materials 0.000 claims abstract description 7
229910052711 selenium Inorganic materials 0.000 claims abstract description 7
229910052714 tellurium Inorganic materials 0.000 claims abstract description 7
229910052740 iodine Inorganic materials 0.000 claims abstract description 6
239000004215 Carbon black (E152) Substances 0.000 claims abstract description 3
229930195733 hydrocarbon Natural products 0.000 claims abstract description 3
229910052799 carbon Inorganic materials 0.000 claims description 43
238000006243 chemical reaction Methods 0.000 claims description 14
150000001875 compounds Chemical class 0.000 claims description 10
229910052794 bromium Inorganic materials 0.000 claims description 6
229910052739 hydrogen Inorganic materials 0.000 claims description 5
125000003545 alkoxy group Chemical group 0.000 claims description 4
125000001183 hydrocarbyl group Chemical group 0.000 claims description 3
150000002430 hydrocarbons Chemical class 0.000 claims 1
150000001299 aldehydes Chemical class 0.000 abstract description 20
239000003054 catalyst Substances 0.000 abstract description 13
150000004945 aromatic hydrocarbons Chemical class 0.000 abstract 1
229910052790 beryllium Inorganic materials 0.000 abstract 1
238000004519 manufacturing process Methods 0.000 abstract 1
230000000737 periodic effect Effects 0.000 abstract 1
230000007704 transition Effects 0.000 abstract 1
239000010948 rhodium Substances 0.000 description 38
238000012360 testing method Methods 0.000 description 30
239000000047 product Substances 0.000 description 27
230000009466 transformation Effects 0.000 description 19
-1 phosphonous acid diester Chemical class 0.000 description 11
KWKAKUADMBZCLK-UHFFFAOYSA-N 1-octene Chemical compound CCCCCCC=C KWKAKUADMBZCLK-UHFFFAOYSA-N 0.000 description 10
JARKCYVAAOWBJS-UHFFFAOYSA-N hexanal Chemical compound CCCCCC=O JARKCYVAAOWBJS-UHFFFAOYSA-N 0.000 description 10
239000002994 raw material Substances 0.000 description 10
125000004429 atom Chemical group 0.000 description 9
JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 description 9
ACVYVLVWPXVTIT-UHFFFAOYSA-M phosphinate Chemical compound [O-][PH2]=O ACVYVLVWPXVTIT-UHFFFAOYSA-M 0.000 description 9
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 7
238000003786 synthesis reaction Methods 0.000 description 6
230000015572 biosynthetic process Effects 0.000 description 5
238000005984 hydrogenation reaction Methods 0.000 description 5
QQONPFPTGQHPMA-UHFFFAOYSA-N propylene Natural products CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 description 5
125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 description 5
229910052703 rhodium Inorganic materials 0.000 description 5
MHOVAHRLVXNVSD-UHFFFAOYSA-N rhodium atom Chemical compound [Rh] MHOVAHRLVXNVSD-UHFFFAOYSA-N 0.000 description 5
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 4
150000002148 esters Chemical class 0.000 description 4
238000006317 isomerization reaction Methods 0.000 description 4
229920001083 polybutene Polymers 0.000 description 4
239000004902 Softening Agent Substances 0.000 description 3
239000002253 acid Substances 0.000 description 3
229910002091 carbon monoxide Inorganic materials 0.000 description 3
239000012018 catalyst precursor Substances 0.000 description 3
239000000460 chlorine Substances 0.000 description 3
238000006471 dimerization reaction Methods 0.000 description 3
238000006170 formylation reaction Methods 0.000 description 3
239000007789 gas Substances 0.000 description 3
238000006384 oligomerization reaction Methods 0.000 description 3
YWAKXRMUMFPDSH-UHFFFAOYSA-N pentene Chemical group CCCC=C YWAKXRMUMFPDSH-UHFFFAOYSA-N 0.000 description 3
150000008301 phosphite esters Chemical class 0.000 description 3
125000004437 phosphorous atom Chemical group 0.000 description 3
238000002360 preparation method Methods 0.000 description 3
150000003254 radicals Chemical class 0.000 description 3
239000011669 selenium Substances 0.000 description 3
230000002195 synergetic effect Effects 0.000 description 3
125000000383 tetramethylene group Chemical group [H]C([H])([*:1])C([H])([H])C([H])([H])C([H])([H])[*:2] 0.000 description 3
238000005829 trimerization reaction Methods 0.000 description 3
BZJTUOGZUKFLQT-UHFFFAOYSA-N 1,3,5,7-tetramethylcyclooctane Chemical group CC1CC(C)CC(C)CC(C)C1 BZJTUOGZUKFLQT-UHFFFAOYSA-N 0.000 description 2
HFDVRLIODXPAHB-UHFFFAOYSA-N 1-tetradecene Chemical compound CCCCCCCCCCCCC=C HFDVRLIODXPAHB-UHFFFAOYSA-N 0.000 description 2
FTZILAQGHINQQR-UHFFFAOYSA-N 2-Methylpentanal Chemical compound CCCC(C)C=O FTZILAQGHINQQR-UHFFFAOYSA-N 0.000 description 2
BKOOMYPCSUNDGP-UHFFFAOYSA-N 2-methylbut-2-ene Chemical compound CC=C(C)C BKOOMYPCSUNDGP-UHFFFAOYSA-N 0.000 description 2
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
UGFAIRIUMAVXCW-UHFFFAOYSA-N Carbon monoxide Chemical compound [O+]#[C-] UGFAIRIUMAVXCW-UHFFFAOYSA-N 0.000 description 2
AMIMRNSIRUDHCM-UHFFFAOYSA-N Isopropylaldehyde Chemical compound CC(C)C=O AMIMRNSIRUDHCM-UHFFFAOYSA-N 0.000 description 2
125000003118 aryl group Chemical group 0.000 description 2
IAQRGUVFOMOMEM-UHFFFAOYSA-N butene Natural products CC=CC IAQRGUVFOMOMEM-UHFFFAOYSA-N 0.000 description 2
125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
229940105305 carbon monoxide Drugs 0.000 description 2
125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 2
150000001735 carboxylic acids Chemical class 0.000 description 2
229910017052 cobalt Inorganic materials 0.000 description 2
239000010941 cobalt Substances 0.000 description 2
GUTLYIVDDKVIGB-UHFFFAOYSA-N cobalt atom Chemical compound [Co] GUTLYIVDDKVIGB-UHFFFAOYSA-N 0.000 description 2
230000022244 formylation Effects 0.000 description 2
230000003993 interaction Effects 0.000 description 2
ZGEGCLOFRBLKSE-UHFFFAOYSA-N methylene hexane Natural products CCCCCC=C ZGEGCLOFRBLKSE-UHFFFAOYSA-N 0.000 description 2
TVMXDCGIABBOFY-UHFFFAOYSA-N n-Octanol Natural products CCCCCCCC TVMXDCGIABBOFY-UHFFFAOYSA-N 0.000 description 2
GYHFUZHODSMOHU-UHFFFAOYSA-N nonanal Chemical compound CCCCCCCCC=O GYHFUZHODSMOHU-UHFFFAOYSA-N 0.000 description 2
OJMIONKXNSYLSR-UHFFFAOYSA-N phosphorous acid Chemical compound OP(O)O OJMIONKXNSYLSR-UHFFFAOYSA-N 0.000 description 2
BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 2
150000003283 rhodium Chemical class 0.000 description 2
RIOQSEWOXXDEQQ-UHFFFAOYSA-N triphenylphosphine Chemical compound C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 RIOQSEWOXXDEQQ-UHFFFAOYSA-N 0.000 description 2
238000005406 washing Methods 0.000 description 2
239000004711 α-olefin Substances 0.000 description 2
DAFHKNAQFPVRKR-UHFFFAOYSA-N (3-hydroxy-2,2,4-trimethylpentyl) 2-methylpropanoate Chemical compound CC(C)C(O)C(C)(C)COC(=O)C(C)C DAFHKNAQFPVRKR-UHFFFAOYSA-N 0.000 description 1
VIHUHUGDEZCPDK-GQCTYLIASA-N (e)-5-methylhept-2-ene Chemical compound CCC(C)C\C=C\C VIHUHUGDEZCPDK-GQCTYLIASA-N 0.000 description 1
LXBJRNXXTAWCKU-SNAWJCMRSA-N (e)-6-methylhept-2-ene Chemical compound C\C=C\CCC(C)C LXBJRNXXTAWCKU-SNAWJCMRSA-N 0.000 description 1
POILWHVDKZOXJZ-ARJAWSKDSA-M (z)-4-oxopent-2-en-2-olate Chemical compound C\C([O-])=C\C(C)=O POILWHVDKZOXJZ-ARJAWSKDSA-M 0.000 description 1
VXNZUUAINFGPBY-UHFFFAOYSA-N 1-Butene Chemical compound CCC=C VXNZUUAINFGPBY-UHFFFAOYSA-N 0.000 description 1
DURPTKYDGMDSBL-UHFFFAOYSA-N 1-butoxybutane Chemical compound CCCCOCCCC DURPTKYDGMDSBL-UHFFFAOYSA-N 0.000 description 1
CRSBERNSMYQZNG-UHFFFAOYSA-N 1-dodecene Chemical group CCCCCCCCCCC=C CRSBERNSMYQZNG-UHFFFAOYSA-N 0.000 description 1
GQEZCXVZFLOKMC-UHFFFAOYSA-N 1-hexadecene Chemical compound CCCCCCCCCCCCCCC=C GQEZCXVZFLOKMC-UHFFFAOYSA-N 0.000 description 1
UNNGUFMVYQJGTD-UHFFFAOYSA-N 2-Ethylbutanal Chemical compound CCC(CC)C=O UNNGUFMVYQJGTD-UHFFFAOYSA-N 0.000 description 1
RCBGGJURENJHKV-UHFFFAOYSA-N 2-methylhept-1-ene Chemical compound CCCCCC(C)=C RCBGGJURENJHKV-UHFFFAOYSA-N 0.000 description 1
QDMFTFWKTYXBIW-UHFFFAOYSA-N 3-Methyl-1-heptene Chemical compound CCCCC(C)C=C QDMFTFWKTYXBIW-UHFFFAOYSA-N 0.000 description 1
ZQDPJFUHLCOCRG-UHFFFAOYSA-N 3-hexene Chemical compound CCC=CCC ZQDPJFUHLCOCRG-UHFFFAOYSA-N 0.000 description 1
YHQXBTXEYZIYOV-UHFFFAOYSA-N 3-methylbut-1-ene Chemical compound CC(C)C=C YHQXBTXEYZIYOV-UHFFFAOYSA-N 0.000 description 1
XTVRLCUJHGUXCP-UHFFFAOYSA-N 3-methyleneheptane Chemical compound CCCCC(=C)CC XTVRLCUJHGUXCP-UHFFFAOYSA-N 0.000 description 1
XZJZVNABSFJYOK-UHFFFAOYSA-N 3-methylidenenonane Chemical compound CCCCCCC(=C)CC XZJZVNABSFJYOK-UHFFFAOYSA-N 0.000 description 1
GLUPFQMLFXGTNL-UHFFFAOYSA-N 3-methyloct-1-ene Chemical compound CCCCCC(C)C=C GLUPFQMLFXGTNL-UHFFFAOYSA-N 0.000 description 1
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
XLWHODVGQQPRHB-UHFFFAOYSA-N C=CCCCC.CC1(CC(C(=O)O)=CC=C1)C(=O)O Chemical compound C=CCCCC.CC1(CC(C(=O)O)=CC=C1)C(=O)O XLWHODVGQQPRHB-UHFFFAOYSA-N 0.000 description 1
0 Cc1cc(O*(c2c(*)c(*)c(*)c(C)c2*)Oc2c(*)cc(*)c(*)c2CCc2c(C)c(C)c(*=C)c(O)c2*=C)c(*)c(*)c1C Chemical compound Cc1cc(O*(c2c(*)c(*)c(*)c(C)c2*)Oc2c(*)cc(*)c(*)c2CCc2c(C)c(C)c(*=C)c(O)c2*=C)c(*)c(*)c1C 0.000 description 1
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 1
239000005977 Ethylene Substances 0.000 description 1
PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 1
VQTUBCCKSQIDNK-UHFFFAOYSA-N Isobutene Chemical group CC(C)=C VQTUBCCKSQIDNK-UHFFFAOYSA-N 0.000 description 1
OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical group [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 1
KJTLSVCANCCWHF-UHFFFAOYSA-N Ruthenium Chemical compound [Ru] KJTLSVCANCCWHF-UHFFFAOYSA-N 0.000 description 1
BUGBHKTXTAQXES-UHFFFAOYSA-N Selenium Chemical compound [Se] BUGBHKTXTAQXES-UHFFFAOYSA-N 0.000 description 1
NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 1
239000005864 Sulphur Substances 0.000 description 1
DHKHKXVYLBGOIT-UHFFFAOYSA-N acetaldehyde Diethyl Acetal Natural products CCOC(C)OCC DHKHKXVYLBGOIT-UHFFFAOYSA-N 0.000 description 1
125000002777 acetyl group Chemical class [H]C([H])([H])C(*)=O 0.000 description 1
125000002252 acyl group Chemical group 0.000 description 1
230000000996 additive effect Effects 0.000 description 1
150000001335 aliphatic alkanes Chemical class 0.000 description 1
125000000217 alkyl group Chemical group 0.000 description 1
125000004390 alkyl sulfonyl group Chemical group 0.000 description 1
WATWJIUSRGPENY-UHFFFAOYSA-N antimony atom Chemical group [Sb] WATWJIUSRGPENY-UHFFFAOYSA-N 0.000 description 1
RQNWIZPPADIBDY-UHFFFAOYSA-N arsenic atom Chemical group [As] RQNWIZPPADIBDY-UHFFFAOYSA-N 0.000 description 1
QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
238000009835 boiling Methods 0.000 description 1
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
239000006227 byproduct Substances 0.000 description 1
239000003795 chemical substances by application Substances 0.000 description 1
230000000052 comparative effect Effects 0.000 description 1
125000004093 cyano group Chemical group *C#N 0.000 description 1
238000006073 displacement reaction Methods 0.000 description 1
230000000694 effects Effects 0.000 description 1
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
230000002349 favourable effect Effects 0.000 description 1
239000011737 fluorine Substances 0.000 description 1
238000005194 fractionation Methods 0.000 description 1
125000000524 functional group Chemical group 0.000 description 1
238000007306 functionalization reaction Methods 0.000 description 1
229910052736 halogen Inorganic materials 0.000 description 1
150000002367 halogens Chemical class 0.000 description 1
238000007172 homogeneous catalysis Methods 0.000 description 1
PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical compound II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 description 1
239000000463 material Substances 0.000 description 1
238000005649 metathesis reaction Methods 0.000 description 1
HZVOZRGWRWCICA-UHFFFAOYSA-N methanediyl Chemical compound [CH2] HZVOZRGWRWCICA-UHFFFAOYSA-N 0.000 description 1
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
AFFLGGQVNFXPEV-UHFFFAOYSA-N n-decene Natural products CCCCCCCCC=C AFFLGGQVNFXPEV-UHFFFAOYSA-N 0.000 description 1
125000001624 naphthyl group Chemical group 0.000 description 1
238000006386 neutralization reaction Methods 0.000 description 1
FBUKVWPVBMHYJY-UHFFFAOYSA-M nonanoate Chemical compound CCCCCCCCC([O-])=O FBUKVWPVBMHYJY-UHFFFAOYSA-M 0.000 description 1
MXRGQMSYIGWYQS-UHFFFAOYSA-N nonanoic acid;rhodium Chemical compound [Rh].CCCCCCCCC(O)=O MXRGQMSYIGWYQS-UHFFFAOYSA-N 0.000 description 1
WWZKQHOCKIZLMA-UHFFFAOYSA-N octanoic acid Chemical compound CCCCCCCC(O)=O WWZKQHOCKIZLMA-UHFFFAOYSA-N 0.000 description 1
150000002902 organometallic compounds Chemical class 0.000 description 1
125000001181 organosilyl group Chemical group [SiH3]* 0.000 description 1
CFHIDWOYWUOIHU-UHFFFAOYSA-N oxomethyl Chemical compound O=[CH] CFHIDWOYWUOIHU-UHFFFAOYSA-N 0.000 description 1
239000001301 oxygen Substances 0.000 description 1
QMMOXUPEWRXHJS-UHFFFAOYSA-N pent-2-ene Chemical group CCC=CC QMMOXUPEWRXHJS-UHFFFAOYSA-N 0.000 description 1
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
150000003003 phosphines Chemical class 0.000 description 1
239000011574 phosphorus Substances 0.000 description 1
229910052697 platinum Inorganic materials 0.000 description 1
239000002243 precursor Substances 0.000 description 1
125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
WHFQAROQMWLMEY-UHFFFAOYSA-N propylene dimer Chemical compound CC=C.CC=C WHFQAROQMWLMEY-UHFFFAOYSA-N 0.000 description 1
239000011541 reaction mixture Substances 0.000 description 1
230000035484 reaction time Effects 0.000 description 1
229910052707 ruthenium Inorganic materials 0.000 description 1
150000003839 salts Chemical class 0.000 description 1
239000002904 solvent Substances 0.000 description 1
238000003756 stirring Methods 0.000 description 1
230000002194 synthesizing effect Effects 0.000 description 1
PORWMNRCUJJQNO-UHFFFAOYSA-N tellurium atom Chemical compound [Te] PORWMNRCUJJQNO-UHFFFAOYSA-N 0.000 description 1
125000001973 tert-pentyl group Chemical group [H]C([H])([H])C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
150000003512 tertiary amines Chemical class 0.000 description 1
229940095068 tetradecene Drugs 0.000 description 1
150000003568 thioethers Chemical class 0.000 description 1
238000012982 x-ray structure analysis Methods 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
- C07C45/49—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reaction with carbon monoxide
- C07C45/50—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reaction with carbon monoxide by oxo-reactions

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Chemical Kinetics & Catalysis (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Catalysts (AREA)

CN00132364A 1999-11-12 2000-11-13 利用配体混合物由烯烃催化制备醛的方法 Pending CN1295997A (zh)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
DE19954510.3		1999-11-12
DE19954510A DE19954510A1 (de)	1999-11-12	1999-11-12	Verfahren zur katalytischen Herstellung von Aldehyden aus Olefinen unter Einsatz von Ligandenmischungen

Publications (1)

Publication Number	Publication Date
CN1295997A true CN1295997A (zh)	2001-05-23

Family

ID=7928840

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CN00132364A Pending CN1295997A (zh)	1999-11-12	2000-11-13	利用配体混合物由烯烃催化制备醛的方法

Country Status (20)

Country	Link
US (1)	US6403837B1 (cs)
EP (1)	EP1099678B1 (cs)
JP (1)	JP2001187759A (cs)
KR (1)	KR20010051634A (cs)
CN (1)	CN1295997A (cs)
AR (1)	AR026425A1 (cs)
AT (1)	ATE234801T1 (cs)
BR (1)	BR0005333A (cs)
CA (1)	CA2325676A1 (cs)
CZ (1)	CZ20004142A3 (cs)
DE (2)	DE19954510A1 (cs)
ES (1)	ES2190932T3 (cs)
ID (1)	ID28360A (cs)
MX (1)	MXPA00011028A (cs)
MY (1)	MY135998A (cs)
PL (1)	PL343792A1 (cs)
SG (1)	SG88797A1 (cs)
TR (1)	TR200003273A2 (cs)
TW (1)	TW538030B (cs)
ZA (1)	ZA200006514B (cs)

Cited By (3)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
CN101681776B (zh) *	2007-04-09	2011-10-05	Lg化学株式会社	含有亚磷酸酯配体的催化剂组合物和使用该催化剂组合物的加氢甲酰化方法
CN105175447A (zh) *	2014-05-20	2015-12-23	赢创工业集团股份有限公司	单亚磷酸酯配体的混合物及其用于催化加氢甲酰基化反应的用途
CN114644652A (zh) *	2022-04-22	2022-06-21	广东欧凯新材料有限公司	一种大位阻双苯酚化合物及其双膦配体的制备方法

Families Citing this family (26)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
DE10058383A1 (de)	2000-11-24	2002-05-29	Oxeno Olefinchemie Gmbh	Neue Phosphininverbindungen und deren Metallkomplexe
DE60304034T2 (de)	2002-03-11	2006-10-12	Union Carbide Chemicals & Plastics Technology Corp., Danbury	Bisphosphit-ligande für carbonylierungsverfahren
DE10210918B4 (de)	2002-03-13	2004-06-03	Oxeno Olefinchemie Gmbh	Verfahren zur Herstellung von Bisphosphiten
DE10220801A1 (de)	2002-05-10	2003-11-20	Oxeno Olefinchemie Gmbh	Verfahren zur Rhodium-katalysierten Hydroformylierung von Olefinen unter Reduzierung der Rhodiumverluste
DE10223593A1 (de) *	2002-05-27	2003-12-11	Degussa	Hydroxydiphosphine und deren Verwendung in der Katalyse
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JP2001187759A (ja)	2001-07-10
ZA200006514B (en)	2001-05-29
TW538030B (en)	2003-06-21
BR0005333A (pt)	2001-07-03
SG88797A1 (en)	2002-05-21
TR200003273A2 (tr)	2001-06-21
MY135998A (en)	2008-07-31
EP1099678A1 (de)	2001-05-16
US6403837B1 (en)	2002-06-11
EP1099678B1 (de)	2003-03-19
ATE234801T1 (de)	2003-04-15
CA2325676A1 (en)	2001-05-12
DE50001482D1 (de)	2003-04-24
CZ20004142A3 (cs)	2002-04-17
PL343792A1 (en)	2001-05-21
AR026425A1 (es)	2003-02-12
DE19954510A1 (de)	2001-05-17
ID28360A (id)	2001-05-17
KR20010051634A (ko)	2001-06-25
MXPA00011028A (es)	2002-05-23

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